(S)-VAPOL hydrogenphosphate
(S)-VAPOL hydrogenphosphate (CAS: 871130-17-5) is a chiral phosphoric acid with the molecular formula C40H25O4P and a molecular weight of 600.60 g/mol. This compound serves as a highly effective catalyst in various asymmetric synthesis applications. Its primary use is in facilitating enantioselective transformations, contributing to the development of stereochemically pure compounds in research and development settings.
- IUPAC
- (S)-2,2′-Diphenyl-3,3′-biphenanthryl-4,4′-diyl phosphate,(S)-VAPOL phosphoric acid,(S)-18-Hydroxy-8,9-diphenyl-diphenanthro[4,3-d:3′,4′-f][1,3,2]dioxaphosphepin-18-oxide
- Synonyms
- (S)-2,2′-Diphenyl-3,3′-biphenanthryl-4,4′-diyl phosphate(S)-VAPOL phosphoric acid(S)-18-Hydroxy-8,9-diphenyl-diphenanthro[4,3-d:3′,4′-f][1,3,2]dioxaphosphepin-18-oxide
Benzoyloxylation of Oxindoles
(S)-VAPOL hydrogenphosphate catalyses the benzoyloxylation of (aryl)oxindoles using benzoyl peroxide, enabling the stereoselective synthesis of valuable intermediates.
Homoaldol Synthesis and Kinetic Resolution
This chiral phosphoric acid is employed in the enantioselective synthesis of homoaldols and the kinetic resolution of existing homoaldols, providing access to chiral building blocks.
Aziridine Ring Opening
It is utilised for the desymmetrization of meso-aziridines through enantioselective ring-opening reactions, yielding chiral amino alcohols.
Aminal Synthesis via Imine Addition
(S)-VAPOL hydrogenphosphate promotes the highly enantioselective addition of imides to imines, producing chiral aminals with excellent stereocontrol.
Friedel-Crafts Reactions
The catalyst facilitates Friedel-Crafts reactions between pyrroles and benzylidenebenzamides, offering a route to substituted indole derivatives.
| Molecular weight | 600.60 |
|---|---|
| Empirical formula | C40H25O4P |
| Optical activity | [α]22/D +412°, c = 1 in chloroform |
| Application | Catalyst for:• Benzoyloxylation of (aryl)oxindoles with benzoyl peroxide1• Enantioselective synthesis of homoaldols and cyclic acetals via kinetic resoln of homoaldols2• Desymmetrization of mono- and bicyclic N-acyl meso-aziridines by ring opening3,4• Highly enantioselective addition of imides to imines to give aminals5• Friedel-Crafts reaction of pyrroles with benzylidenebenzamides6 |
| Melting point | >400 °C |
| Protective equipment | Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter |
|---|---|
| Water hazard class (WGK, DE) | 3 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is (S)-VAPOL hydrogenphosphate used for?
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(S)-VAPOL hydrogenphosphate is primarily used as a chiral catalyst in asymmetric synthesis, including benzoyloxylation of oxindoles, enantioselective synthesis of homoaldols, desymmetrization of aziridines, and addition of imides to imines.
What is the CAS number and formula for (S)-VAPOL hydrogenphosphate?
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The CAS number for (S)-VAPOL hydrogenphosphate is 871130-17-5, and its empirical formula is C40H25O4P.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies (S)-VAPOL hydrogenphosphate as a research-grade chemical. We do not represent it as meeting USP, BP, EP, or other pharmacopoeial standards.
How should (S)-VAPOL hydrogenphosphate be handled safely?
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Handling requires appropriate personal protective equipment, including eyeshields and gloves. A type N95 (US) or type P1 (EN143) respirator filter should be used if airborne exposure is possible. It is classified under WGK 2 in Germany.
How is (S)-VAPOL hydrogenphosphate shipped and exported?
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Tech Serve Solutions, as a specialist global supplier and exporter, ships and exports (S)-VAPOL hydrogenphosphate in compliance with all relevant international regulations for chemical transport.
How can I request a sample or quote for (S)-VAPOL hydrogenphosphate?
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To request a sample or a quotation for (S)-VAPOL hydrogenphosphate, please contact our sales department through the TSS website or by direct inquiry.
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